Unorthodox PM wisdom: Automating user insights, unselling job candidates, logging every decision, more | Kevin Yien (Stripe, Square, Mutiny)

**Kevin Yien** (0:00)
The PM job can become a little too internal, influencing my stakeholders and getting alignment and all these things. But if you can't sell or support your own product, I don't trust you to build the product.

**Lenny Rachitsky** (0:10)
You think every PM should keep a decision log.

**Kevin Yien** (0:13)
We all talk about product sense. To me, it's just a fancy way of saying, you can make good decisions with insufficient data. PMs need as many reps as possible in making decisions, documenting the rationale behind those decisions, and then crucially, seeing the outcome of them.

**Lenny Rachitsky** (0:28)
We have a lot of interesting approaches to hiring, including this idea of unsell email.

**Kevin Yien** (0:31)
When you get to offer stage, I send an email and I say all the terrible things that are probably going to reinforce their fears. If you can tell them that upfront and they can read that whole email and still be equally excited to join, you find yourself any plus higher.

**Lenny Rachitsky** (0:45)
I'm curious if you found any interesting uses of AI in your work.

**Kevin Yien** (0:49)
We are not even beneath the dust on the surface when it comes to what's going to change.

**Lenny Rachitsky** (1:00)
Today, my guest is Kevin Yien. Kevin leads product for Merchant Experiences at Stripe. Before that, he built the restaurant business and the ecosystem teams at Square, and most recently was head of product and design at Mutiny. He also makes ice cream, and as you'll hear in their conversation, was a pretty competitive eater for some part of his life. In our conversation, Kevin shares a ton of unique and insightful perspectives on how to be a successful product manager, including how to get into product management, how to improve your relationship with your engineers and designers, a bunch of advice on hiring, why you should keep a decision log, how to automate your customer research, plus a ton of really powerful stories around failure and AI and career. This episode is for anyone looking to become a better leader, thinker, and builder of products. If you enjoy this podcast, don't forget to subscribe and followed in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes, and it helps the podcast tremendously. With that, I bring you Kevin Yien. Kevin, thank you so much for being here, and welcome to the podcast.

**Kevin Yien** (2:03)
Thanks Lenny, I am humbled to be here.

**Lenny Rachitsky** (2:05)
I've been a big fan of yours from afar. I've been following you on Twitter for a long time. You have a very distinct profile photo that I feel like you maybe not haven't changed for a long time. How long have you had this profile?

**Kevin Yien** (2:15)
Oh gosh, probably 2011 or 2012 The story behind that is I was inspired actually by Chris Dixon's avatar at the time, and I wanted something really similar to it, but I couldn't figure out how to. Luckily, I was dating a designer at the time. And so she made me that sort of custom pick that has been my profile since then, and she's not my wife.

**Lenny Rachitsky** (2:40)
Oh my god. Funny enough, I had a startup idea once where it's like a profile picture as a service business, where there's like these three tiers where it's like one is automated, one is someone illustrates, and one is like a professional photo as like feels like everyone. Profile photos are so important. Totally. I never follow through. Probably not a good business anyway.

**Kevin Yien** (2:59)
But a good idea. A good tool.

**Lenny Rachitsky** (3:00)
Good idea. Thank you. Thank you for making me feel better. I've been looking forward to this conversation for a long time. As I said, I've been a big fan of yours for a long time.
Something that I've noticed about you is you have a lot of really unique perspectives on a lot of different things, and in particular, product management. How to be successful as a PM, how to get into product management, things like that. So I thought it'd be fun to start there, talking through some of these things that I've heard you talk about, and then get into some very tactical stuff that you've found to be useful in your product management career. The first thing that I've heard you talk about is that you discourage people from going straight into product management if they want to become product managers, you encourage them to start somewhere else first. Why is that? Where do you think people should start? Talk about this insight that you've had. Yeah.

**Kevin Yien** (3:45)